What I’d do the same or differently

Apr 5, 2021

Issue #125—April 2, 2021
It was 23 years ago this month that I walked away from my senior-level marketing role at Phillips Publishing to become a freelance copywriter.

And what a ride it’s been!

I’m so grateful I made the decision to focus on copywriting and enjoy the higher earnings, passive income, and most importantly, the freedom and flexibility that came with going freelance.

Over the past few years, I’ve gradually shifted from doing less and less copywriting to doing much more teaching and mentoring, including putting out this e-letter.

It’s to the point that I’m seriously considering making it “official” that I’m retiring from copywriting (I’m not sure I’m there yet…I’m still keeping multiple controls alive while taking on select projects here and there.)

But this morning I did a little reflecting on what I’d do the same–and what I’d differently–if I was starting out as a freelance copywriter today.

And I thought I’d share that with you today, as it could help guide you as you build or launch your own copywriting career.

Two things I’d do the same:

1) Work at a top direct-response company before going freelance. When I applied for a job as a Marketing Manager at Phillips Publishing, I had never heard of it.

I’d worked at another company before that and had been exposed to direct marketing and had written copy. But joining Phillips opened up a whole new world. It was an incredible learning opportunity to be in the thick of everything.

I got the chance to learn about copy and promo tactics that were working, got more experienced people to look at my copy and provide feedback, and was in an atmosphere that encouraged risk-taking–allowing me to try new things and discover what worked (and what didn’t).

I learned at least 10 or 100 times more just in the first year or two working there than I did in my previous marketing positions or from getting my MBA in marketing.

More importantly, I made countless valuable connections that opened doors for me when I went freelance. There were industry contacts that became clients. And there were dozens of Phillips colleagues who referred me to clients after I left. The company itself also became one of my best clients!

I’m glad that I left the company on good terms, without burning any bridges. I’m also glad that a year or so earlier, I refused to sign a non-compete (despite the stock incentives that were offered with it).

This gave me the freedom I needed to best leverage my publishing and supplement experience right from the start…and earn 50% more than my previous six-figure job during my first year of freelancing.

2) Get experience with running a business or having P&L (profit and loss) responsibility, or otherwise analyzing marketing data and results. I’d had plenty exposure in previous marketing positions prior to Phillips (I’d done everything from SAS programming to building marketing databases to launching new products and working as a brand manager).

But the advantage of working at such a results-driven company as Phillips, and with direct marketing being so measurable, gave me an incredibly valuable training ground for my future freelance copywriting career.

And the icing on the cake, of course, was having the opportunity while at Phillips to launch and run their Healthy Directions supplement business, and grow it to more than $23 million in sales ($38 million in today’s dollars) within the first 3 years.

Getting up close to the numbers and having P&L responsibility opened my eyes to how to not only write successful copy, but how to craft offers, maximize the “back end” of a business, mine hidden “gold” and build customer relationships, experiment with new tactics and channels by testing smart, and so much more.

Being able to bring that kind of marketing background and expertise to the table when writing promos and campaigns for my clients has given me a huge edge…and it can do the same for you. In fact, it’s probably more important than ever these days in today’s hyper-competitive markets.

Okay, now let’s look at…

Two things I’d do differently:

1) Find a copywriting mentor early on. When I first went freelance, aside from a six-month retainer deal that acted as a “bridge”, I was pretty much on my own. I was figuring it all out as I went along, drawing on the experience I gained at Phillips and Healthy Directions.

I yearned to break into writing long-form promos and be able to earn royalties, just like the legendary (and not so well-known) copywriters Phillips used to hire. Someone I knew who had left Phillips had made the leap before me and was raking in huge controls and royalties…but he’d had much more exposure to long-form copy.

So when I finally was able to win some of these long-coveted assignments, it would have been much easier if I’d had a mentor to help show me the way. It could have saved me from some of my most painful early “bombs”, though with a few of them I was able to turn them into huge winners on the second try.

For one of those initial “bombs” though, it was getting feedback from a more experienced copywriter on what had gone wrong that led to the reworked version I wrote that became a 10-year control (that paid plenty of royalties along the way).

I was also able to get feedback at times on my copy in my early years from top copywriters like Bob Bly, Don Hauptmann, and David Deutsch…who generously reviewed my copy and refused payment (I plied them with huge fruit baskets and other gifts instead).

There were advantages, though, to going it on my own. I was able to build a reputation early on for the big winners I did write. I wasn’t “hidden” behind a bigger name as an understudy, unable to take full credit. I built my own direct relationships with clients.

And I didn’t have to pay my “dues” by signing any contracts or NDAs that would force me to provide my copywriting services at rock-bottom fees in a form of indentured servitude…or not be allowed to share what I knew or learned with others.

For me, having already established myself in many ways and gained valuable experience, it wasn’t as important to make these kinds of trade-offs in order to work with a mentor. But if I had been just starting out without these advantages, they may have been worth it…or perhaps wouldn’t be required with the right mentor.

2) Look for opportunities to put myself “out there” early on. Up until about 4 or 5 years ago, I sort of hid myself away and quietly knocked out control after control for clients. I didn’t seek out the stage, write blog posts or articles, or put myself out there as an expert.

Honestly, I was content for many years to work no more than 20 to 25 hours a week while my kids were at school, then call it a day and run them to their many activities, and take at least a month or two off each year for vacations.

That was my dream life…my “why”…and I found I was able to achieve the elusive “work-life balance” while, as a certain copywriting training organization likes to say, “earning more than most doctors”.

But my kids grew up and became more independent (the #1 job of parenting!) And I noticed I was getting tired of only using one side of my brain–the writing side–and not the marketing side, which I had always enjoyed so much.

About 4 years ago at a copywriting event I met Ben Settle, and he pulled me aside to ask why–with all my experience in writing controls and beating legends like Jim Rutz–that I didn’t have my own courses and training? Honestly I had really thought about doing it.

But next thing I knew, I started writing emails, building a list, and here we are.

I’ve gotten better known, I’ve built a business where I get to use my “mad marketing skillz” once again and keep learning new things…and most importantly, I’ve gained the satisfaction of helping other copywriters succeed in a freelancing career that’s been so very good to me.

Now I see other copywriters putting themselves “out there” as experts much earlier than I did (including some of my recent mentees). And there’s something about teaching others that helps you master it even more yourself.

Not only that, with so many more copywriters you’re “competing” against, it’s a way to make sure you stand out.

It’s something I could have started doing at least a decade or more earlier…but for me, I’m happy with where I decided to put my focus at that point in time. Your situation and goals may be different.

That’s all I’ve got today…I’m looking forward to taking the rest of the day off and enjoying a relaxing holiday weekend. I hope you enjoy yours, too!

Yours for smarter marketing,


P.S. I thought I’d share this fun bit of memorabilia from when my last day at Healthy Directions (I left to go to another division of Phillips and work with Jay Abraham and Denis Waitley).

My employees put together this mock cover of our supplement catalog and presented it to me. Every cover line and bit of copy is part of an “inside joke” (let’s see if you can “get” them). It still makes me laugh out loud whenever I see it…